Former colonial societies, largely categorized as the Third World, are still affected by negative retentions of their colonial past. The education system in these societies is arguably the most affected in this regard; and teacher education is no exception. Since teacher training is such a pivotal component of this sector, it is a key point of entry to gain a deeper understanding of the effects of colonialism on educational institutions, structures and processes. Jamaica provides an important context for this study in light of its dual or two-tiered system of education which evolved from slavery and colonialism. Using both phenomenological and postcolonial theoretical frameworks, I conducted a study to ascertain what the experiences of Jamaican teachers' college lecturers would reveal about the status of teacher education. Using an in-depth interviewing methodology, I interviewed 17 lecturers from five (5) of the six (6) teachers' colleges in Jamaica. Each interview was approximately 90 minutes long, and each participant was interviewed thrice. Interviews were audiotaped and transcribed verbatim. I judiciously read each interview transcript, and then coded segments that were salient to my research focus---the lived experience of Jamaican teachers' college lecturers. These coded segments indicated nine (9) themes which overwhelmingly suggest that as tertiary institutions, teachers' colleges are viewed in low regard and continue to occupy the lower rung of an inequitable two-tiered system. In keeping with the second theoretical frame of the study---postcolonial discourse---I analyzed six (6) of the themes with a view to uncovering deeper meanings underlying the educators' experiences. The preponderance of the meanings derived strongly suggests that there are retentions of colonialism that prevent teachers' colleges from cementing their place as legitimate tertiary institutions. However, there is some measure of hope, as the findings also indicate that there are pockets of radical pedagogical shifts among teachers' college lecturers, away from hegemonic conceptions of teaching rooted in British colonialism and imperialism.